The series has a dark, yet humorous tone to it, but it also really earns the name.
- The first real stinger would have to be in The Reptile Room when Uncle Monty is discovered dead.
- Klaus being struck across the face by Olaf in the first book, then breaking down in tears with his sisters once Olaf and his goons leave the room. The series has a lot of absurd and outlandish moments throughout the thirteen books, but that one moment where Klaus is struck across the face by someone who is supposed to love and care for him and his sisters is very sadly realistic and can strike a chord with many people who have gone through the same experience.
- It's also the moment the children realize that Count Olaf is just as bad - and probably worse - than they feared and that this is not a matter of looking on the bright side; their situation is truly terrible.
- Lemony, whose betrothed left him for a mutual friend; she was happy and had three children, then died at the hands of an old acquaintance. Lemony then made it his life's work to document the sufferings of said children, to write down all they had lost, and that he had lost with them.
- The end of The Austere Academy. Just as Olaf has been revealed... again, the Baudelaires watch as Duncan and Isadora are taken away by Olaf's cronies. The Quagmires are their first genuine friends they've had in a long time and they're suddenly taken away from them.
- Lemony recounting how he once went to a masquerade ball and for once felt happy due to hiding who he was from others. He then painfully mentions how he tried to approach Beatrice and tell her that she and Bertrand were in danger...only to cut halfway and admit it's too painful to recite. For such a Lovable Coward, you pity poor Mr. Snicket.
- The fact that The Austere Academy and The Unauthorized Autobiography (when put together) imply that Lemony was at a masked ball that killed Beatrice and that she didn't die in the fire that killed her husband (as Snicket mentions people are looking for Monty's reptiles, setting it after book 2) but never got to reunite with her children anyway due to being burned alive in that fire instead.
- Lemony recounting how he once went to a masquerade ball and for once felt happy due to hiding who he was from others. He then painfully mentions how he tried to approach Beatrice and tell her that she and Bertrand were in danger...only to cut halfway and admit it's too painful to recite. For such a Lovable Coward, you pity poor Mr. Snicket.
- At the beginning of The Hostile Hospital, the Baudelaires have a moment to summarize all the trouble they’re in and all the trouble they’ve been through. They’re stranded alone, lost, and unlike every time before that they had to leave a new place they’re convicts and they can’t even rely on Mr. Poe to come take them somewhere new. There isn’t any immediate danger (except dying of thirst), so they can’t even distract themselves from their awful situation by working on a way out. The siblings face a collective Heroic BSoD until Puck brings them a way out.
- In The Slippery Slope, two of the most important codes of VFD derive from the same poem: Algernon Charles Swinburne's The Garden of Proserpine. The codes themselves are quite sadnote but knowing the context of the poem makes it worse: the poem is an ode of gratitude that the afterlife is a silent, empty place untouched by emotion. Given how many members have been touched by death, the symbolism of the Great Unknown, and how the prequel series reveals the quiet fatalism that true members of the organization carry, it is sad, but perhaps not surprising that they would choose this poem as one of their key texts.
- At the end of The Grim Grotto, when Fiona tells Klaus to think of her when he thinks of his favorite food.
- The "denouement" of The Penultimate Peril - and indeed of the whole series really - is utterly devastating. The court case turns out to be a total farce, two of the three judges turn out to be evil villains whom we have previously met. The Baudelaires have no choice but to help Olaf escape. And then Sunny suggests that if they burn down the hotel, it will aid their escape (and act as a signal that "the last safe place is safe no more.") We don't really know, but it is implied that this kills perhaps hundreds of people.
- And before the "denouement", the Baudelaire children have a moment with Olaf in which they try and convince him that he can be a good guy. Surprisingly, Olaf doesn't answer them with snark or insults. Instead, he answers with a quiet "What else can I do?"
- Spoken by Sunny in The Penultimate Peril: "The last safe place is safe no more."
- Also by Sunny, in The End: "If we fail, at least we die reading together."
- The End: The title of the last book, but the story itself subverts the notion of endings, by pointedly refusing to answer any of the questions or resolve any of the plot threads that built up over the course of the series, and while resolving the story after a fashion, consciously skirting any feeling of satisfaction or closure. The title even could've been The Enigmatic End to preserve alliteration.
- In The End when Kit is trapped on the makeshift raft, in labor, and the series' long-running villain, Count Olaf, lifts her off and kisses her "One last time." Then, with a bit of darkly humorous poetry, he gives one final "HA!" and dies from a harpoon injury. The Baudelaire children then help Kit give birth to a healthy baby girl, who they name after their mother. Kit dies in childbirth, and the author gives a beautiful speech about the moral ambiguities of life and ends the story on the usual mysterious note. Then, comes the epilogue chapter, where the Baudelaires are preparing to leave the island for good after one year. They constructed a boat, and named the boat, like the baby, after their late mother, Beatrice. For background, all the book have been dedicated to the narrator's long-lost love, Beatrice, and he regularly includes little shout-outs to her in the text. The revelation in the end that the children he's writing about were hers explains why he wrote the books all by itself.
- Also in The End, where The Beatrice Letters and other material hints that the Baudelaire orphans may have survived, there's no sign that the Quagmire Triplets, Fiona or Fernald survived aside from some reports from the Daily Punctilio. Quigley was reunited with his siblings only for all of them to die (and none of them got to reunite with the Baudelaires). Fiona and Fernald reunited and were turning to side of good, with Fiona especially wanting to make it back to Klaus to apologize, only to die with her brother before she can make it to him.
- Don't forget poor decent folks like Hector, who wasn't even involved in any of this VFD nonsense, died by coming into contact with the Great Unknown.
- The painful stanza from "This be the verse" by Philip Larkin:
- Man hands on misery to man
It deepens like a coastal shelf.
Get out as early as you can
and don't have any kids yourself.
- Then when the Baudelaires visit Count Olaf's grave and sit there silently, beyond words.
- The fact that the boat that they left the island on was named Beatrice is especially important if you read The Beatrice Letters, a companion to the series. There are punch-out letters which are supposed to give a message to the reader once they've been unscrambled. The message: BEATRICE SANK. Tears ensued. Still, the books occasionally mention what the Baudelaires thought when looking back on events years afterwards, so at least one of them must have survived somehow.
